N-(2-aminoethyl)acetamide → HCID 19095285, compound

HRID 486521Notes

Reaction equation

HRID 486521 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][CH2:11][CH:12]2OCCO2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:18]([NH:21][CH2:22][CH2:23][NH2:24])(=[O:20])[CH3:19]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:24]([CH2:23][CH2:22][NH:21][C:18](=[O:20])[CH3:19])[CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 66082N-(2-aminoethyl)acetamideHCID 2758094HCID 2758094, compound

Product 1

HCID 19095285HCID 19095285, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

3',4'-Dichloro-3-(1,3-dioxolan-2-yl)propiophenone (10.0 g) was dissolved in 20 ml of acetic acid and added under argon and while stirring to a solution of 7.4 g of N-acetylethylenediamine in 80 ml of acetic acid. The reaction mixture was heated to reflux overnight, the acetic acid was subsequently removed in a vacuum. The residue was taken up in 200 ml of methylene chloride and washed with a mixture of 100 ml of saturated sodium hydrogen carbonate solution and 100 ml of 2N sodium hydroxide solution. The aqueous phase was back-extracted twice with 100 ml of methylene chloride each time, the organic phases were combined, dried with MgSO4 and freed from solvent. The residue, 12.5 g of dark brown oil were chromatographed on 500 g of silica gel with ethyl acetate as the eluent. 9.1 g (84%) of N-[2-[2-(3,4-dichlorophenyl)-pyrrol-1-yl]ethyl]acetamide were isolated as a yellow-brown oil. MS: m/e=296, 298, 300 (9:6:1, M+).

Workup

  1. additionadded under argon
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux overnight
  4. customthe acetic acid was subsequently removed in a vacuum
  5. washwashed with a mixture of 100 ml of saturated sodium hydrogen carbonate solution and 100 ml of 2N sodium hydroxide solution
  6. extractionThe aqueous phase was back-extracted twice with 100 ml of methylene chloride each time
  7. dry with materialdried with MgSO4
  8. customThe residue, 12.5 g of dark brown oil were chromatographed on 500 g of silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-4f9f1a9482f942e395d6b969785917a3
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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